Two of the biggest questions that we are always asking ourselves is, “what should I be doing with my life to make money?” Second, “what can I do to make money that I will enjoy?” We all have to do something to make money in order to live, and we don’t want to get stuck with a job we don’t like. Alan Watts, a famous Philosophy professor and writer from the mid 20th Century has a famous lecture on youtube called “What do you desire?” In this lecture he asks the question, “If money were no object, how would you spend your life?” In other words, is it really worth it to spend our lives doing something that we don’t like doing just for the money? What would we spend our lives doing if getting a paycheck wasn’t so important? And whatever that is, do that, and forget about the money and eventually it will come. Watts raises great questions to ask ourselves, and as a skateboarder and a writer, they are thoughts that I resonate with and get inspired by. When someone is really passionate about something the dream is to always find a way to make money doing that someday. Whether it be music, writing, photography, bodybuilding, some entrepreneurial idea, making little crafts and selling them on Etsy, and so on. And the thought of having to get a “real job,” something that is completely unrelated to this passion, because we need to make more money than our passion is bringing in, makes our heart sick and often makes these jobs feel like a burden that we can’t wait to shed. Our goal in life is always to “make it” in whatever it is that gets us excited to get out of bed in the morning.

When we hear things like, “if money were no object, how would you spend your life?” We tend to get all inspired and jump to things like, “well I would make music all day, or write books, or minister to kids, or become an entrepreneur,” which are good things to think about. But in our pursuit of trying to “make it,” we find ourselves unable to make anything happen and have no money, we often bang our head against the wall trying to figure out a way to make it work, which in turn makes money into an object all over again, just in a different way. Instead of getting a job we don’t like doing, we make the thing we hope to make into a job stressful and full of angst, which used to be just pure fun and joy. Which leads me to ask the question, “Have we really picked a better life for ourselves in these pursuits?” If it were so, would I have all this stress and anxiety over writing a best selling book and having a thriving writing career? All this pursuing a life where money is no object sounds all fine and dandy until rent is due, or when we are well into our thirties still as broke as we’ve ever been because we refused to get a good job or find a trade, because that would be “putting too much emphasis on money.” We want to be happy and live a life full of passion and fun, not have a boring job that is all about the money. My wife and I met a guy at a Starbucks in LA a while ago that moved there from South Africa decades ago in order to become a performing artist. He was probably in his fifties or sixties and has been homeless for years, still hanging on to his dream of making it in Hollywood. After meeting this guy, I had to ask myself, is this an admirable way to live? Complete, utter devotion to a dream even if it means we spend our lives on the streets of LA begging for money? When does the pursuit of “making it,” become delusion? When is it time to maybe think about a trade we could learn that can still allow us to spend a little time with our passions? All the glamorizing of turning passion into paychecks, complete with all its cliche’s and sayings like, “love what you do and you’ll never work a day in your life,” may at times be doing more harm than good. The scariest part about this encounter with this man, is that how I have lived my life I could easily become this guy. All my decisions have always been based on fun and passion. Doing what I love and forgetting about the money, believing that one day the money will come. Never taking the time to learn any kind of trade that could take care of finances. If we never think about money and just live for fun and passion, this homeless man in LA could very easily be the trajectory of our life. There has to be a balance and a middle ground here where we can take care of finances while crafting whatever passion or artistic skill we hope to make an income with someday.

I had a dream once that my sister was telling me, speaking about my nephew (her son), “you know, you live like you have already made it, Jordan is constantly trying to make it as a basketball player or as a skateboarder and he lives with constant anxiety because of it.” In reality this dream would be flipped. I am the one constantly living with the anxiety of trying to make it and Jordan is the content, level-headed 18 year old. I have meditated on this dream for years, and am always asking myself, what would it look like to live as if I have already made it? Do I forget about the money? Do I forget about the passion? Or is it some combination of the two? I have come to the conclusion that it would be finding a way to enjoy life and being content with how life currently is, and not having to live with the constant anxiety of, “if I don’t make it soon, I may become homeless or living with my parents again.” And if that means having a day job and doing my passions on the side when I can find the time, so be it. I don’t have to be a published writer or a professional skateboarder to be happy, because the truth is, even if I had that stuff I will most likely still find ways to not be happy. The real feat of the human condition is that we have become masters of finding ways to not be happy no matter how much success and glory we have attained. If we can’t be happy and content now, what makes us think we will be “then?” Peter McWilliams, a philosophy writer said, “I see nothing wrong with desire… but if you must have it in order to be happy, then you are denying the happiness of the here and now.” The “when I…then I” game is one of perpetual putting off the joy of today until tomorrow, and as the cliche goes, “tomorrow never comes.” If we can’t be happy now, we will never be happy then.

Passions are a good thing, and should be pursued, they give us life and get us excited to get out of bed, but I have noticed an epidemic with a lot of young people (myself included) that we somehow became convinced that the passion pursuit always has to come with a devotion to poverty until we make it? it is either “starving artist” or “successful artist.” There doesn’t seem to be much middle ground. We have become convinced that learning some kind of trade or getting a good job is like “selling out” where once we have it, it means we will have to throw out our passions and become boring nine to fivers. But the reality is, if we can pay our bills without stress, it removes the anxiety of trying to make it. We can just enjoy them and not have to worry about making money from them. I may never make it as a writer, but that doesn’t mean I ever have to stop writing. No matter what I do to make money, I can always write. Why should I feel that getting a good job means I have to stop writing? Or that I need to be writing for a living to be happy? Is doing it just because I love it not enough? Somehow we got sold on this nonsense that if we aren’t doing something with our passion that makes us money than we are failing at life, and we need to hold out on getting a good job as long as we can or we will never make it in what we really want to do and therefore never be happy. If we feel like we need to “make it” to be happy than we are in for a rude awakening, for nobody ever truly makes it. When we live in that world we will always lack something that we feel like we need to be happy. As English novelist and chemist C.P. Snow said, “The pursuit of happiness is a most ridiculous phrase: if you pursue happiness you’ll never find it.” If we can’t have joy and contentment in our current situation, then we will never find it in a future one. Pulling our hair out because we just can’t seem to make enough money and make it happen is not a sustainable way to live. There is a balance between living as our grandparents did of doing whatever we have to do to make money and forgetting about our passions, and the millennial of forgetting about what we have to do to make money and just pursuing our passions. The breakdown in our spirits comes when we feel like we have to give ourselves fully to either one or the other. We have to find a way to do both, to have a job that makes decent money without forgoing our passions in life.